4-Pentenal → 1,8-Nonadien-5-ol

HRID 16225

Reaktionsgleichung

Reaktionsgleichung von HRID 16225
[CH2:1]([Mg]Br)[CH2:2][CH:3]=[CH2:4].[CH:7](=[O:12])[CH2:8][CH2:9][CH:10]=[CH2:11]>O1CCCC1>[CH2:4]=[CH:3][CH2:2][CH2:1][CH:7]([OH:12])[CH2:8][CH2:9][CH:10]=[CH2:11]

Komponenten

4

Edukt 2

HCID 164184-PentenalHCID 178418797HCID 178418797, Verbindung

Produkt 1

HCID 118295421,8-Nonadien-5-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-Butenyl-magnesium bromide (125 mL, 0.5 M in tetrahydrofuran, 62.5 mmol) was added drop wise to a stirred and cooled (−78° C.) solution of pent-4-enal (4 g, 48.07 mmol) in dry tetrahydrofuran (160 mL). After the addition, the solution was warmed to room temperature and then quenched with NH4Cl solution. The mixture was partitioned with diethyl ether and the organic phase was washed with brine, dried (MgSO4), filtered, and evaporated. The residue was purified over silica gel using 5-15% diethyl ether in hexanes to give the title compound as an oil.

Aufarbeitung

  1. additionAfter the addition
  2. customquenched with NH4Cl solution
  3. customThe mixture was partitioned with diethyl ether
  4. washthe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified over silica gel using 5-15% diethyl ether in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e98f6149fafa44c789cdbd4327d485dc
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737137B2

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